# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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#######################################################################

data_twin5
_database_code_depnum_ccdc_archive 'CCDC 1559817'
_audit_update_record             
;
2017-07-03 deposited with the CCDC.
2018-05-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H30 F6 Fe N6 O2 Sb'
_chemical_formula_weight         582.02

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.7459(7)
_cell_length_b                   9.9165(7)
_cell_length_c                   14.9643(13)
_cell_angle_alpha                83.487(3)
_cell_angle_beta                 89.016(3)
_cell_angle_gamma                75.755(3)
_cell_volume                     1106.84(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5962
_cell_measurement_theta_min      3.0112
_cell_measurement_theta_max      26.3568

_exptl_crystal_description       Tabullar
_exptl_crystal_colour            Black
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.746
_exptl_crystal_F_000             582
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    1.944
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6982
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            4428
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.011
_diffrn_reflns_theta_max         26.387
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             4428
_reflns_number_gt                4272
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0621P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4428
_refine_ls_number_parameters     260
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0295
_refine_ls_R_factor_gt           0.0279
_refine_ls_wR_factor_ref         0.0984
_refine_ls_wR_factor_gt          0.0929
_refine_ls_goodness_of_fit_ref   1.193
_refine_ls_restrained_S_all      1.193
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8025(8) 0.0579(6) 0.5661(4) 0.0282(12) Uani 1 1 d . . . . .
H1A H 0.9167 0.0395 0.5982 0.042 Uiso 1 1 calc R U . . .
H1B H 0.8094 0.1122 0.5078 0.042 Uiso 1 1 calc R U . . .
H1C H 0.7760 -0.0311 0.5567 0.042 Uiso 1 1 calc R U . . .
C2 C 0.4912(7) 0.1681(6) 0.5683(4) 0.0278(12) Uani 1 1 d . . . . .
H2A H 0.4603 0.0800 0.5608 0.042 Uiso 1 1 calc R U . . .
H2B H 0.5059 0.2171 0.5091 0.042 Uiso 1 1 calc R U . . .
H2C H 0.3959 0.2271 0.6006 0.042 Uiso 1 1 calc R U . . .
C3 C 0.6462(6) 0.0520(5) 0.7072(3) 0.0180(10) Uani 1 1 d . . . . .
H3A H 0.6868 -0.0486 0.6992 0.022 Uiso 1 1 calc R U . . .
H3B H 0.5206 0.0709 0.7267 0.022 Uiso 1 1 calc R U . . .
C4 C 0.7589(6) 0.0864(4) 0.7775(4) 0.0174(9) Uani 1 1 d . . . . .
H4A H 0.7440 0.0332 0.8360 0.021 Uiso 1 1 calc R U . . .
H4B H 0.8859 0.0589 0.7608 0.021 Uiso 1 1 calc R U . . .
C5 C 0.8315(6) 0.2780(6) 0.8473(3) 0.0204(11) Uani 1 1 d . . . . .
H5A H 0.9539 0.2199 0.8411 0.024 Uiso 1 1 calc R U . . .
H5B H 0.7948 0.2619 0.9105 0.024 Uiso 1 1 calc R U . . .
C6 C 0.8280(7) 0.4299(6) 0.8235(3) 0.0227(11) Uani 1 1 d . . . . .
H6A H 0.7087 0.4880 0.8366 0.027 Uiso 1 1 calc R U . . .
H6B H 0.9164 0.4552 0.8612 0.027 Uiso 1 1 calc R U . . .
C7 C 0.8082(7) 0.6126(5) 0.6984(4) 0.0255(12) Uani 1 1 d . . . . .
H7A H 0.6798 0.6444 0.7079 0.038 Uiso 1 1 calc R U . . .
H7B H 0.8336 0.6304 0.6343 0.038 Uiso 1 1 calc R U . . .
H7C H 0.8715 0.6636 0.7333 0.038 Uiso 1 1 calc R U . . .
C8 C 1.0639(6) 0.4164(6) 0.7148(3) 0.0214(11) Uani 1 1 d . . . . .
H8A H 1.1230 0.4717 0.7486 0.032 Uiso 1 1 calc R U . . .
H8B H 1.0903 0.4316 0.6507 0.032 Uiso 1 1 calc R U . . .
H8C H 1.1074 0.3168 0.7365 0.032 Uiso 1 1 calc R U . . .
C9 C 0.5192(6) 0.2849(5) 0.8171(3) 0.0131(9) Uani 1 1 d . . . . .
H9A H 0.4380 0.2821 0.7673 0.016 Uiso 1 1 calc R U . . .
H9B H 0.4985 0.3838 0.8289 0.016 Uiso 1 1 calc R U . . .
C10 C 0.4683(6) 0.2012(5) 0.9009(3) 0.0148(9) Uani 1 1 d . . . . .
H10A H 0.4735 0.1045 0.8880 0.018 Uiso 1 1 calc R U . . .
H10B H 0.5539 0.1961 0.9502 0.018 Uiso 1 1 calc R U . . .
C11 C 0.2850(7) 0.3925(6) 0.9716(4) 0.0291(12) Uani 1 1 d . . . . .
H11A H 0.1632 0.4346 0.9896 0.044 Uiso 1 1 calc R U . . .
H11B H 0.3272 0.4600 0.9292 0.044 Uiso 1 1 calc R U . . .
H11C H 0.3631 0.3671 1.0248 0.044 Uiso 1 1 calc R U . . .
C12 C 0.2201(7) 0.1675(6) 0.9911(4) 0.0280(12) Uani 1 1 d . . . . .
H12A H 0.2934 0.1439 1.0461 0.042 Uiso 1 1 calc R U . . .
H12B H 0.2258 0.0823 0.9626 0.042 Uiso 1 1 calc R U . . .
H12C H 0.0963 0.2093 1.0063 0.042 Uiso 1 1 calc R U . . .
F1 F 0.3568(4) 0.6340(3) 0.7877(3) 0.0299(7) Uani 1 1 d . . . . .
F2 F 0.0685(4) 0.8261(4) 0.7223(3) 0.0609(14) Uani 1 1 d . . . . .
F3 F 0.1740(6) 0.8237(5) 0.8898(3) 0.0646(14) Uani 1 1 d . . . . .
F4 F 0.2104(4) 1.0287(3) 0.7656(3) 0.0393(10) Uani 1 1 d . . . . .
F5 F 0.4953(4) 0.8365(4) 0.8313(2) 0.0326(7) Uani 1 1 d . . . . .
F6 F 0.3910(5) 0.8395(4) 0.6646(2) 0.0343(8) Uani 1 1 d . . . . .
Fe1 Fe 0.72768(8) 0.34006(6) 0.65122(4) 0.01171(15) Uani 1 1 d . . . . .
N1 N 0.5355(5) 0.4616(4) 0.6236(3) 0.0173(8) Uani 1 1 d . . . . .
N2 N 0.8763(6) 0.3341(5) 0.5662(3) 0.0216(9) Uani 1 1 d . . . . .
N3 N 0.6595(5) 0.1383(4) 0.6202(3) 0.0181(8) Uani 1 1 d . . . . .
N4 N 0.7070(5) 0.2374(4) 0.7859(3) 0.0128(7) Uani 1 1 d . . . . .
N5 N 0.8683(5) 0.4603(4) 0.7279(3) 0.0154(8) Uani 1 1 d . . . . .
N6 N 0.2873(5) 0.2681(4) 0.9287(3) 0.0188(9) Uani 1 1 d . . . . .
O1 O 0.4231(5) 0.5500(4) 0.5868(3) 0.0290(9) Uani 1 1 d . . . . .
O2 O 0.9454(6) 0.3629(5) 0.4983(3) 0.0448(11) Uani 1 1 d . . . . .
Sb1 Sb 0.28147(4) 0.83064(3) 0.77711(2) 0.01891(11) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N3 1.483(6) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 N3 1.478(7) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 N3 1.491(6) . ?
C3 C4 1.498(7) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 N4 1.471(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 N4 1.497(6) . ?
C5 C6 1.502(8) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 N5 1.473(6) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 N5 1.485(6) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 N5 1.486(5) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 N4 1.498(5) . ?
C9 C10 1.525(6) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 N6 1.471(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 N6 1.450(7) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 N6 1.472(6) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
F1 Sb1 1.881(3) . ?
F2 Sb1 1.867(3) . ?
F3 Sb1 1.869(4) . ?
F4 Sb1 1.893(3) . ?
F5 Sb1 1.873(3) . ?
F6 Sb1 1.875(3) . ?
Fe1 N1 1.693(4) . ?
Fe1 N2 1.697(4) . ?
Fe1 N4 2.175(4) . ?
Fe1 N5 2.217(4) . ?
Fe1 N3 2.288(4) . ?
N1 O1 1.167(5) . ?
N2 O2 1.179(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 C1 H1A 109.5 . . ?
N3 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N3 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N3 C2 H2A 109.5 . . ?
N3 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N3 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N3 C3 C4 109.9(4) . . ?
N3 C3 H3A 109.7 . . ?
C4 C3 H3A 109.7 . . ?
N3 C3 H3B 109.7 . . ?
C4 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
N4 C4 C3 110.2(4) . . ?
N4 C4 H4A 109.6 . . ?
C3 C4 H4A 109.6 . . ?
N4 C4 H4B 109.6 . . ?
C3 C4 H4B 109.6 . . ?
H4A C4 H4B 108.1 . . ?
N4 C5 C6 109.3(4) . . ?
N4 C5 H5A 109.8 . . ?
C6 C5 H5A 109.8 . . ?
N4 C5 H5B 109.8 . . ?
C6 C5 H5B 109.8 . . ?
H5A C5 H5B 108.3 . . ?
N5 C6 C5 111.5(4) . . ?
N5 C6 H6A 109.3 . . ?
C5 C6 H6A 109.3 . . ?
N5 C6 H6B 109.3 . . ?
C5 C6 H6B 109.3 . . ?
H6A C6 H6B 108.0 . . ?
N5 C7 H7A 109.5 . . ?
N5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N5 C8 H8A 109.5 . . ?
N5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N4 C9 C10 116.2(4) . . ?
N4 C9 H9A 108.2 . . ?
C10 C9 H9A 108.2 . . ?
N4 C9 H9B 108.2 . . ?
C10 C9 H9B 108.2 . . ?
H9A C9 H9B 107.4 . . ?
N6 C10 C9 110.0(4) . . ?
N6 C10 H10A 109.7 . . ?
C9 C10 H10A 109.7 . . ?
N6 C10 H10B 109.7 . . ?
C9 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
N6 C11 H11A 109.5 . . ?
N6 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N6 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N6 C12 H12A 109.5 . . ?
N6 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N6 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1 Fe1 N2 111.3(2) . . ?
N1 Fe1 N4 109.41(16) . . ?
N2 Fe1 N4 139.30(18) . . ?
N1 Fe1 N5 100.91(18) . . ?
N2 Fe1 N5 92.09(18) . . ?
N4 Fe1 N5 80.67(15) . . ?
N1 Fe1 N3 102.07(18) . . ?
N2 Fe1 N3 92.40(18) . . ?
N4 Fe1 N3 78.69(14) . . ?
N5 Fe1 N3 153.12(15) . . ?
O1 N1 Fe1 164.7(4) . . ?
O2 N2 Fe1 161.6(5) . . ?
C2 N3 C1 107.8(4) . . ?
C2 N3 C3 110.5(4) . . ?
C1 N3 C3 108.8(4) . . ?
C2 N3 Fe1 111.5(3) . . ?
C1 N3 Fe1 110.1(3) . . ?
C3 N3 Fe1 108.2(3) . . ?
C4 N4 C5 111.4(4) . . ?
C4 N4 C9 112.6(3) . . ?
C5 N4 C9 109.9(4) . . ?
C4 N4 Fe1 105.4(3) . . ?
C5 N4 Fe1 108.8(3) . . ?
C9 N4 Fe1 108.6(3) . . ?
C6 N5 C7 110.7(4) . . ?
C6 N5 C8 109.4(4) . . ?
C7 N5 C8 108.1(4) . . ?
C6 N5 Fe1 106.8(3) . . ?
C7 N5 Fe1 110.9(3) . . ?
C8 N5 Fe1 110.9(3) . . ?
C11 N6 C10 111.2(4) . . ?
C11 N6 C12 109.8(4) . . ?
C10 N6 C12 109.2(4) . . ?
F2 Sb1 F3 90.1(2) . . ?
F2 Sb1 F5 179.47(17) . . ?
F3 Sb1 F5 90.2(2) . . ?
F2 Sb1 F6 90.5(2) . . ?
F3 Sb1 F6 179.15(17) . . ?
F5 Sb1 F6 89.10(15) . . ?
F2 Sb1 F1 90.85(15) . . ?
F3 Sb1 F1 90.88(17) . . ?
F5 Sb1 F1 89.53(14) . . ?
F6 Sb1 F1 89.65(15) . . ?
F2 Sb1 F4 89.97(15) . . ?
F3 Sb1 F4 89.94(18) . . ?
F5 Sb1 F4 89.64(15) . . ?
F6 Sb1 F4 89.52(16) . . ?
F1 Sb1 F4 178.84(13) . . ?

_refine_diff_density_max         0.874
_refine_diff_density_min         -1.040
_refine_diff_density_rms         0.229

_shelxl_version_number           2014/6


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_chemical_properties_physical    ', Oxygen-sensitive'
